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Maligned "pharma bro" Marin Shkreli shed tears as he made a final plea to the judge who handed down his 7-year prison sentence in a New York courtroom on spanking eroticismFriday afternoon for securities and wire fraud charges.

Reporters for Vice, Bloomberg, and WCBS reported Shkreli's remorse for his many, many actions that have led to one of the biggest examples of schadenfreude we've seen in quite some time.

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The Associated Press also confirmed Shkreli's contrite sobs, reporting:

"Pharma Bro" Martin Shkreli is crying as he tells a judge preparing to sentence him that he made many mistakes.

The pharmaceutical executive apologized to investors he defrauded in a securities fraud conviction.

U.S. District Judge Kiyo Matsumoto, though saying she believed he was remorseful, mentioned some of his more recent misdeeds, referencing both Shkreli's harassment of journalist Lauren Duca (which got him banned from Twitter), and that time Shkreli offered people money for Hillary Clinton's hair, which Matsumoto previously called a "solicitation of assault."

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Ultimately, Shkreli's apology did little to deter Matsumoto from handing down the 7 year sentence, which was a little less than half of what prosecutors had recommended; he reportedly faced a maximumsentence of 45 years.

Shkreli first came to incur the world's ire, and earned that derogatory "Pharma Bro" nickname, in 2015 when, as head of Turing Pharmaceuticals, he raised the cost of the drug Daraprim, used to treat parasitic infections in HIV patients, from $13.50-per-pill to $750-per-pill and showed little remorse for it.

There's also Shkreli's long, twisted tale involving an extremely rare Wu-Tang Clan album and having a donation made to Bernie Sanders' 2016 presidential campaign rejected by the candidate himself.

All that said, Judge Matsumoto said at the sentencing she did not take these into account when deciding Shkreli's sentence, focusing instead on the crimes he was found guilty of.

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Still, Shkreli leaves a long trail of bad karma and angry people -- including his own lawyer -- in his wake that aren't sad to see him to go to prison for fraud. Whether or not he'll be changed by his time in prison, we'll just have to wait and see.

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